EP0286971A2 - Colorants diazacyanine cationiques - Google Patents

Colorants diazacyanine cationiques Download PDF

Info

Publication number
EP0286971A2
EP0286971A2 EP88105503A EP88105503A EP0286971A2 EP 0286971 A2 EP0286971 A2 EP 0286971A2 EP 88105503 A EP88105503 A EP 88105503A EP 88105503 A EP88105503 A EP 88105503A EP 0286971 A2 EP0286971 A2 EP 0286971A2
Authority
EP
European Patent Office
Prior art keywords
dyes
formula
cationic
mixtures
diaza
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP88105503A
Other languages
German (de)
English (en)
Other versions
EP0286971A3 (en
EP0286971B1 (fr
Inventor
Alfred Dr. Brack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0286971A2 publication Critical patent/EP0286971A2/fr
Publication of EP0286971A3 publication Critical patent/EP0286971A3/de
Application granted granted Critical
Publication of EP0286971B1 publication Critical patent/EP0286971B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/18—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having three nitrogen atoms as the only ring hetero atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • the invention relates to cationic diazacyanine dyes of the formula wherein R represents methyl or ethyl and X ⁇ stand for a colorless anion, their mixtures with the isomeric dyes of the formula wherein R and X ⁇ have the meaning given above, and processes for dyeing polyacrylonitrile and polyacrylonitrile-wool blends using these dyes.
  • Preferred anions are methosulfate, hydrogen sulfate, chloride, bromide and chlorozincate.
  • Cationic diazacyanine dyes which are obtained by coupling diazotized 3-amino-1,2,4-triazole with an alkylbenzylaniline and subsequent quaternization and are known, for example, from US Pat. Nos. 2,883,373 and 3,438,963, are widely known used for dyeing polyacrylonitrile. However, they are only of limited stability against hydrolyzing and reducing influences in the dyebath. In particular when dyeing polyacrylonitrile / wool mixtures, such influences lead to the partial destruction of the dye.
  • the dyes of the formula (I) and their mixtures with the dyes of the formula (II) have a high stability in the dyebath compared to the known dyes and are excellent for dyeing polyacrylonitrile in polyacrylonitrile-wool mixtures own.
  • the methosulfates of the dyes according to the invention are notable for good crystallizability. They remain free-flowing during storage even without the addition of zinc chloride necessary in the case of the known dyes mentioned, so that the undesirable contamination of the dyeing waste water by zinc ions is avoided.
  • the dye bases or their hydrogen sulfates can advantageously be prepared by simultaneous coupling in sulfuric acid with aqueous sodium nitrite solution.
  • the isolation of the color bases or a hydrogen salt can be avoided if the simultaneous coupling is carried out with sodium nitrite in acetic acid and then methylated with dimethyl sulfate. No additional alkali is required.
  • the sodium acetate formed from the sodium nitrite is sufficient.
  • the amount corresponding to 185 g of dry azobase is stirred with so much water that a total of 370 g of water are present.
  • 30.8 g of magnesium oxide are introduced with good cooling at a maximum of 5 ° C.
  • the pH bet should be 9.5-9.6.
  • 185 g of dimethyl sulfate are added dropwise at 0-5 ° C. in the course of 2 h, the mixture is then stirred for a further 4 h at 0-5 ° C. and the temperature is then allowed to rise to room temperature. After finished Methylation (TLC control), the mixture is heated to 60-80 ° C. for about 1 h to destroy residual dimethyl sulfate.
  • the zinc chloride double salt or chlorozincate can be separated by adding zinc chloride or hydrochloric acid zinc chloride solution, and the bromide of the dye in crystalline form by adding NaBr in 80% yield (based on ethyl-benzyl-m-toluidine).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
EP88105503A 1987-04-15 1988-04-07 Colorants diazacyanine cationiques Expired - Lifetime EP0286971B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3712822 1987-04-15
DE3712822 1987-04-15
DE19873722322 DE3722322A1 (de) 1987-04-15 1987-07-07 Kationische diazacyaninfarbstoffe
DE3722322 1987-07-07

Publications (3)

Publication Number Publication Date
EP0286971A2 true EP0286971A2 (fr) 1988-10-19
EP0286971A3 EP0286971A3 (en) 1989-11-29
EP0286971B1 EP0286971B1 (fr) 1992-07-29

Family

ID=25854692

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88105503A Expired - Lifetime EP0286971B1 (fr) 1987-04-15 1988-04-07 Colorants diazacyanine cationiques

Country Status (4)

Country Link
US (1) US4840641A (fr)
EP (1) EP0286971B1 (fr)
JP (1) JPS63268769A (fr)
DE (2) DE3722322A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011085906A1 (de) * 2011-11-08 2013-05-08 Henkel Ag & Co. Kgaa Zwitterionische Azofarbstoffe zum Färben von keratinhaltigen Fasern

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438963A (en) * 1966-02-07 1969-04-15 American Cyanamid Co Alkylation process for cationic triazole dye
EP0036505A2 (fr) * 1980-03-11 1981-09-30 Bayer Ag Procédé de préparation de colorants cationiques ainsi que leur utilisation pour la teinture de fibres synthétiques modifiées par traitement acide
US4364738A (en) * 1980-08-01 1982-12-21 Ciba-Geigy Corporation Crystalline bromide or iodide salts of triazole dyes for polyacrylonitrile
DE3602587A1 (de) * 1986-01-29 1987-07-30 Hoechst Ag Verfahren zur herstellung von hochkonzentrierten farbstoffloesungen kationischer farbstoffe

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT555665B (fr) * 1955-01-28
DE2355076A1 (de) * 1973-11-03 1975-05-07 Bayer Ag Kationische farbstoffe
EP0012053B1 (fr) * 1978-11-30 1982-02-17 P C U K Produits Chimiques Ugine Kuhlmann Solutions aqueuses concentrées de colorant cationique, leur procédé de préparation et leur utilisation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438963A (en) * 1966-02-07 1969-04-15 American Cyanamid Co Alkylation process for cationic triazole dye
EP0036505A2 (fr) * 1980-03-11 1981-09-30 Bayer Ag Procédé de préparation de colorants cationiques ainsi que leur utilisation pour la teinture de fibres synthétiques modifiées par traitement acide
US4364738A (en) * 1980-08-01 1982-12-21 Ciba-Geigy Corporation Crystalline bromide or iodide salts of triazole dyes for polyacrylonitrile
DE3602587A1 (de) * 1986-01-29 1987-07-30 Hoechst Ag Verfahren zur herstellung von hochkonzentrierten farbstoffloesungen kationischer farbstoffe

Also Published As

Publication number Publication date
DE3722322A1 (de) 1988-11-03
DE3873135D1 (de) 1992-09-03
JPS63268769A (ja) 1988-11-07
EP0286971A3 (en) 1989-11-29
US4840641A (en) 1989-06-20
EP0286971B1 (fr) 1992-07-29

Similar Documents

Publication Publication Date Title
DE2945537A1 (de) Kupferkomplex-formazanverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
EP0286971B1 (fr) Colorants diazacyanine cationiques
EP0120399B1 (fr) Procédé de préparation de colorants acides de la série des triphénylméthanes, pauvres en électrolytes
DE2700996C3 (de) Pyrazolin-Verbindungen
DE2509622A1 (de) Loesungen von azomethinfarbstoffen und verfahren zur herstellung gelber, basischer azomethinfarbstoffe
EP0229980B1 (fr) Procédé de préparation de colorants hydrazoniques cationiques
DE2142947C3 (de) Wasserlösliche 2-Phenylbenzthiazol-Monoazofarbstoffe und deren Verwendung zum Färben von Papier
DE3602587C2 (fr)
DE2001748A1 (de) Verfahren zur Herstellung von konzentrierten Loesungen kationischer Farbstoffe
DE2733178B1 (de) Verfahren zur Herstellung von Chlorzinksalzen von Benzthiazoliumazofarbstoffen
EP0144701B1 (fr) Procédé de préparation de dérivés de 2-amino-1-hydroxy-4- ou 5-(bêta-sulfatoéthylsulfonyl)-benzène et leur utilisation pour la synthèse de composés réactifs aux fibres
EP0005172B1 (fr) Dérivés de la coumarine et leur application comme azurants pour matériaux organiques de poids moléculaire élevé
DE2311072C3 (de) Ammoniumsalze sulfonsäuregruppenhaltiger Farbstoffe, ihre Herstellung und Verwendung zum Färben von Papier
EP0019577B1 (fr) Solutions de colorants hautement concentrées, leur préparation et utilisation et préparations de colorants à partir de ces solutions
DE889498C (de) Verfahren zur Herstellung saurer Wollfarbstoffe
EP0042556A2 (fr) Procédé de préparation de colorants alkylaryl-hydrazoniques cationiques et de leurs bases de colorants
DE1965384A1 (de) Verfahren zur Herstellung von p-Nitroso- und p-Nitrophenolen
AT207381B (de) Verfahren zur Herstellung von neuer Pyrviniumsalze der Pamoinsäure
DE1811230C3 (de) Verfahren zur Herstellung von 1,4-Diamino-2-acetylanthrachinonen
EP0603129A1 (fr) Colorants oxaziniques, procédé de leur préparation et leur utilisation
AT67674B (de) Verfahren zur Darstellung von Kernnitrosoderivaten der Phenylglyzin-o-karbonsäure und ihrer sauren und neutralen Ester.
AT223724B (de) Verfahren zur Herstellung von neuen Cyaninfarbstoffen
DE587509C (de) Faerbepraeparate
DE3705386A1 (de) Verfahren zur herstellung eines blauen anthrachinoiden dispersionsfarbstoffs
DE1815219C3 (de) Lichtempfindliche wässrige Lösung und ihre Verwendung zur Herstellung von wärmeentwickelbaren Zweikomponenten-Diazotypiemateri alien

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19880407

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE FR GB LI

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): CH DE FR GB LI

17Q First examination report despatched

Effective date: 19910430

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): CH DE FR GB LI

REF Corresponds to:

Ref document number: 3873135

Country of ref document: DE

Date of ref document: 19920903

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)
ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20010315

Year of fee payment: 14

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20021101

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20070328

Year of fee payment: 20

REG Reference to a national code

Ref country code: CH

Ref legal event code: PFA

Owner name: BAYER AKTIENGESELLSCHAFT

Free format text: BAYER AKTIENGESELLSCHAFT# #D-51368 LEVERKUSEN (DE) -TRANSFER TO- BAYER AKTIENGESELLSCHAFT# #D-51368 LEVERKUSEN (DE)

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20070404

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20070411

Year of fee payment: 20

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20080406

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20080406